Oprah Winfrey

The media mogul purchased the 4,607-square foot, three-bedroom Beaux Arts-style apartment in 2006 for $5.6 million -- more than twice the price at which she resold this summer. Located in the East Lake Shore Drive District, she never resided in the unit herself, which includes a wine room, wood-paneled library and solarium. Winfrey also has a spacious duplex nearby and a 23-acre Montecito, Calif. estate called Promised Land which she picked up for $50 million in 2001.